NPASS Compound

Natural Product: NPC480082

Natural Product ID	NPC480082
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DRGQUZHGHUOBPW-QESRWVAYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44584189
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 109110 0 0 0 0 0 0 0 0999 V2000 -13.8325 2.2184 -0.9518 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.2457 1.2162 -1.9464 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5153 0.1675 -1.1285 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4013 0.8121 -0.3066 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7289 -0.2789 0.4808 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5995 0.2636 1.3378 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5830 0.8928 0.4490 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9679 -0.0577 -0.5718 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2956 -1.1552 0.1732 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6025 -2.1985 -0.5830 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5067 -1.9308 -1.5091 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2739 -1.2885 -1.0485 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2807 0.1096 -0.5695 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8515 0.4331 -0.1540 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7072 1.8576 0.2986 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2271 2.0086 0.7012 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3367 1.6990 -0.4046 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5501 0.7162 -0.3453 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7283 -0.1474 0.8115 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0888 -0.1258 1.4542 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1892 -0.5643 0.5475 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5508 -0.5364 1.2540 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6268 -1.4729 2.4055 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3901 -2.6477 1.8869 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8357 -2.2445 0.5225 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3921 -2.2724 0.5137 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8731 -1.2698 1.4923 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2470 -1.1069 1.8609 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3720 -0.7240 1.0563 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9060 -1.4153 -0.0870 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3498 -1.5245 -1.4310 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2995 -0.2530 -2.1997 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5192 0.8802 -1.7647 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0817 2.0741 -1.4491 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0360 3.0283 -1.0429 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2465 3.4391 0.4022 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8389 2.3520 -1.2327 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0944 1.0696 -1.6257 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2185 0.2091 -1.8315 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4699 -0.9423 0.3290 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3279 0.3035 -0.5550 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0010 0.2147 -1.2435 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5861 1.0211 -1.5940 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.7958 2.6313 -1.2932 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1443 3.0721 -0.7693 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.0440 1.6998 0.0269 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.0950 0.7167 -2.4565 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6209 1.7065 -2.6964 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0856 -0.5759 -1.8071 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2197 -0.2875 -0.4249 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8714 1.4933 0.4614 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7389 1.4146 -0.9252 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3490 -1.0510 -0.1937 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4525 -0.7333 1.1928 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1959 -0.5443 1.9560 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9933 1.1016 1.9898 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6930 1.2740 1.0305 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9433 1.7736 -0.1036 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2028 0.5536 -1.0897 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7513 -0.4234 -1.2708 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7718 -0.7369 1.0530 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1828 -1.7099 0.7067 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3809 -2.8958 -1.0623 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1752 -2.9201 0.2068 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1848 -2.9535 -1.9233 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8363 -1.4215 -2.4650 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8385 -1.9582 -0.2332 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5074 -1.4114 -1.8826 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9524 0.2876 0.2572 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5673 -0.2408 0.6520 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3710 2.1446 1.1095 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8698 2.5367 -0.5581 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1171 1.4464 1.6148 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1221 3.1074 0.9898 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4119 2.3068 -1.3119 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1724 0.5652 -1.2534 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0061 -0.1023 1.6073 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6204 -1.2179 0.4104 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2338 0.9357 1.8051 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1181 -0.7259 2.3818 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0650 -1.5797 0.1461 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7564 0.5137 1.5737 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6529 -1.8648 2.7719 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0983 -0.9785 3.2870 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1766 -2.9330 2.5909 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7221 -3.5659 1.8409 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4603 -2.9486 -0.2481 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6300 -3.3213 0.7989 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6610 -2.0786 -0.5309 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2742 -1.3515 2.4744 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4399 -0.2515 1.1281 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6060 -2.1020 2.4188 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2681 -0.3895 2.8067 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2072 0.3851 0.7148 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2556 -0.5045 1.8196 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0325 -1.0967 -0.1703 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1131 -2.5313 0.2445 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4559 -2.1466 -1.5384 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1375 -2.1592 -2.0707 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4015 0.0413 -2.3485 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9696 -0.5358 -3.2665 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1407 2.3134 -1.4821 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1249 3.9426 -1.7044 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2923 3.7787 0.5307 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6025 4.2939 0.6916 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0735 2.5973 1.0720 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2288 0.1383 -0.9223 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3013 0.7801 -1.9770 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8867 1.8669 -1.1919 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 2 0 25 40 1 0 21 41 1 0 14 42 1 0 13 43 1 0 40 22 1 0 38 33 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 9 61 1 0 9 62 1 0 10 63 1 0 10 64 1 0 11 65 1 0 11 66 1 0 12 67 1 0 12 68 1 0 13 69 1 1 14 70 1 1 15 71 1 0 15 72 1 0 16 73 1 0 16 74 1 0 17 75 1 0 18 76 1 0 19 77 1 0 19 78 1 0 20 79 1 0 20 80 1 0 21 81 1 6 22 82 1 1 23 83 1 0 23 84 1 0 24 85 1 0 24 86 1 0 25 87 1 0 26 88 1 0 26 89 1 0 27 90 1 0 27 91 1 0 28 92 1 0 28 93 1 0 29 94 1 0 29 95 1 0 30 96 1 0 30 97 1 0 31 98 1 0 31 99 1 0 32100 1 0 32101 1 0 34102 1 0 35103 1 0 36104 1 0 36105 1 0 36106 1 0 41107 1 0 42108 1 0 43109 1 0 M END

Standard InCHIKey	DRGQUZHGHUOBPW-QESRWVAYSA-N
Standard InCHI	InChI=1S/C37H66O6/c1-3-4-5-6-7-8-9-10-14-19-24-33(38)34(39)25-20-15-16-21-26-35(40)36-28-27-32(43-36)23-18-13-11-12-17-22-31-29-30(2)42-37(31)41/h15-16,29-30,32-36,38-40H,3-14,17-28H2,1-2H3/b16-15-/t30?,32?,33-,34-,35+,36+/m0/s1
SMILES	CCCCCCCCCCCC[C@@H]([C@H](CC/C=CCC[C@H]([C@H]1CCC(CCCCCCCC2=CC(C)OC2=O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	606.49	Volume:	676.227 ? Van der Waals volume.
Dense:	0.897	LogP:	7.602 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.586 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.461 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	27.0	Rigid Bonds:	12.0
TPSA:	96.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	2.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.049	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.585	Fsp³:	0.865
MCE-18:	30.029 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.698	Fluc inhibitor:	0.148 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.052 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.023 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.591	Promiscuous compounds:	0.058

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.079	MDCK Permeability:	-4.772
Pgp-inhibitor:	0.001	Pgp-substrate:	0.005
PAMPA:	0.01 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.547
20% Bioavailability (F20%):	0.939	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.804
Plasma Protein Binding (PPB):	98.758%	Volume Distribution (VD):	0.975
Fu:	0.995% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.992
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.548
BSEP inhibitor:	0.99

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	0.008	CYP2C19-substrate:	0.027
CYP2C9-inhibitor:	0.468	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.337	CYP2D6-substrate:	0.994
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.292 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

5.409

Half-life (T1/2):

1.13

ADMET: Toxicity

hERG Blockers:	0.508	hERG Blockers (10um):	0.872
Human Hepatotoxicity (H-HT):	0.481	Drug-induced Liver Injury (DILI):	0.018
AMES Toxicity:	0.061	Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.514	Skin Sensitization:	1.0
Carcinogencity:	0.071	Eye Corrosion:	0.07
Eye Irritation:	0.757	Respiratory Toxicity:	0.61
Drug-induced Neurotoxicity:	0.012	Ototoxicity:	0.647
Hematotoxicity:	0.024	Drug-induced Nephrotoxicity:	0.739
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.053
A549 Cytotoxicity:	0.914	Hek293 Cytotoxicity:	0.315
BCF:	0.861 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.741 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.247 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.384 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO40783	Annona coriaceae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778244]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	2

Activity Type	# Activity
Cell line	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell line	Vero	Chlorocebus aethiops	ED50	=	5.0	10'-2 ug/ml	PMID[8778244]
NPT91	Cell line	KB	Homo sapiens	ED50	=	6.0	10'-4 ug/ml	PMID[8778244]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC480082 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	17429
0.1-0.2	29356
0.2-0.3	2735
0.3-0.4	112
0.4-0.5	48
0.5-0.6	86
0.6-0.7	66
0.7-0.8	0
0.8-0.85	1
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9423	High Similarity	NPC253801
0.8868	High Similarity	NPC322529
0.88	High Similarity	NPC65930
0.8627	High Similarity	NPC329615
0.8182	Intermediate Similarity	NPC480081
0.7885	Intermediate Similarity	NPC241360
0.7885	Intermediate Similarity	NPC293136
0.75	Intermediate Similarity	NPC320458
0.7451	Intermediate Similarity	NPC329829
0.7358	Intermediate Similarity	NPC607439
0.7333	Intermediate Similarity	NPC279267
0.7321	Intermediate Similarity	NPC258068
0.7321	Intermediate Similarity	NPC476583
0.7143	Intermediate Similarity	NPC473478
0.7143	Intermediate Similarity	NPC473651
0.7143	Intermediate Similarity	NPC66346
0.7018	Intermediate Similarity	NPC231096
0.7018	Intermediate Similarity	NPC475581
0.7018	Intermediate Similarity	NPC283085
0.7018	Intermediate Similarity	NPC62118
0.7018	Intermediate Similarity	NPC132496
0.7018	Intermediate Similarity	NPC107717
0.7018	Intermediate Similarity	NPC488252
0.6909	Remote Similarity	NPC219652
0.6909	Remote Similarity	NPC473840
0.6863	Remote Similarity	NPC73310
0.6863	Remote Similarity	NPC473529
0.6863	Remote Similarity	NPC180363
0.6863	Remote Similarity	NPC94875
0.6863	Remote Similarity	NPC11332
0.6863	Remote Similarity	NPC145914
0.6863	Remote Similarity	NPC601174
0.6863	Remote Similarity	NPC601403
0.6863	Remote Similarity	NPC603568
0.6863	Remote Similarity	NPC604330
0.6863	Remote Similarity	NPC608300
0.6863	Remote Similarity	NPC611200
0.6863	Remote Similarity	NPC611571
0.6735	Remote Similarity	NPC609415
0.6724	Remote Similarity	NPC473995
0.6724	Remote Similarity	NPC606740
0.6724	Remote Similarity	NPC608614
0.6667	Remote Similarity	NPC473520
0.6667	Remote Similarity	NPC329838
0.6667	Remote Similarity	NPC600188
0.6607	Remote Similarity	NPC25703
0.6481	Remote Similarity	NPC25764
0.6481	Remote Similarity	NPC235809
0.6481	Remote Similarity	NPC39279
0.6481	Remote Similarity	NPC475159
0.6481	Remote Similarity	NPC39167
0.6481	Remote Similarity	NPC131002
0.6481	Remote Similarity	NPC292809
0.6481	Remote Similarity	NPC202055
0.6481	Remote Similarity	NPC473780
0.6481	Remote Similarity	NPC604521
0.6481	Remote Similarity	NPC606804
0.6481	Remote Similarity	NPC607425
0.6481	Remote Similarity	NPC608574
0.6429	Remote Similarity	NPC600524
0.6429	Remote Similarity	NPC608355
0.6393	Remote Similarity	NPC91067
0.6379	Remote Similarity	NPC309211
0.6379	Remote Similarity	NPC20621
0.6379	Remote Similarity	NPC318963
0.6379	Remote Similarity	NPC485250
0.6379	Remote Similarity	NPC605101
0.6333	Remote Similarity	NPC477014
0.6333	Remote Similarity	NPC477013
0.625	Remote Similarity	NPC156804
0.614	Remote Similarity	NPC473156
0.614	Remote Similarity	NPC163093
0.614	Remote Similarity	NPC144415
0.614	Remote Similarity	NPC282815
0.614	Remote Similarity	NPC600956
0.614	Remote Similarity	NPC608157
0.6066	Remote Similarity	NPC233551
0.6066	Remote Similarity	NPC40376
0.6066	Remote Similarity	NPC21208
0.6034	Remote Similarity	NPC473671
0.6034	Remote Similarity	NPC475268
0.6034	Remote Similarity	NPC470400
0.6034	Remote Similarity	NPC77871
0.6034	Remote Similarity	NPC9678
0.6034	Remote Similarity	NPC319036
0.6034	Remote Similarity	NPC605867
0.6032	Remote Similarity	NPC473905
0.6032	Remote Similarity	NPC477015
0.6	Remote Similarity	NPC477012
0.5932	Remote Similarity	NPC132940
0.5902	Remote Similarity	NPC169511
0.5902	Remote Similarity	NPC287164
0.5902	Remote Similarity	NPC234077
0.5893	Remote Similarity	NPC100921
0.5893	Remote Similarity	NPC477018
0.5862	Remote Similarity	NPC134865
0.5862	Remote Similarity	NPC488246
0.5862	Remote Similarity	NPC103523
0.5862	Remote Similarity	NPC488627
0.5862	Remote Similarity	NPC480080
0.5862	Remote Similarity	NPC488631
0.5862	Remote Similarity	NPC477011
0.5862	Remote Similarity	NPC610454
0.5833	Remote Similarity	NPC20533
0.5833	Remote Similarity	NPC488250
0.5833	Remote Similarity	NPC605396
0.5738	Remote Similarity	NPC69082
0.5738	Remote Similarity	NPC488249
0.5645	Remote Similarity	NPC120398
0.5645	Remote Similarity	NPC471567
0.5593	Remote Similarity	NPC473649
0.5593	Remote Similarity	NPC154097
0.5593	Remote Similarity	NPC159750
0.5593	Remote Similarity	NPC73248
0.5593	Remote Similarity	NPC470401
0.5522	Remote Similarity	NPC482766
0.55	Remote Similarity	NPC604764
0.5439	Remote Similarity	NPC606043
0.5397	Remote Similarity	NPC488244
0.5385	Remote Similarity	NPC280612
0.5345	Remote Similarity	NPC107986
0.5345	Remote Similarity	NPC223871
0.5345	Remote Similarity	NPC231009
0.5345	Remote Similarity	NPC103284
0.5345	Remote Similarity	NPC110710
0.5345	Remote Similarity	NPC1083
0.5345	Remote Similarity	NPC82795
0.5345	Remote Similarity	NPC286338
0.5345	Remote Similarity	NPC603931
0.5345	Remote Similarity	NPC604237
0.5323	Remote Similarity	NPC477010
0.5294	Remote Similarity	NPC477017
0.5294	Remote Similarity	NPC477016
0.5254	Remote Similarity	NPC488253
0.5254	Remote Similarity	NPC473669
0.5254	Remote Similarity	NPC488251
0.5224	Remote Similarity	NPC473663
0.5224	Remote Similarity	NPC473723
0.5224	Remote Similarity	NPC475173
0.5167	Remote Similarity	NPC81045
0.5167	Remote Similarity	NPC232555
0.5167	Remote Similarity	NPC39754
0.5167	Remote Similarity	NPC171135
0.5167	Remote Similarity	NPC171174
0.5167	Remote Similarity	NPC182383
0.5167	Remote Similarity	NPC114694
0.5167	Remote Similarity	NPC61257
0.5167	Remote Similarity	NPC320569
0.5167	Remote Similarity	NPC485248
0.5167	Remote Similarity	NPC133730
0.5167	Remote Similarity	NPC191929
0.5167	Remote Similarity	NPC142117
0.5167	Remote Similarity	NPC100454
0.5167	Remote Similarity	NPC242364
0.5167	Remote Similarity	NPC480249
0.5167	Remote Similarity	NPC172821
0.5167	Remote Similarity	NPC485249
0.5167	Remote Similarity	NPC274446
0.5167	Remote Similarity	NPC485251
0.5167	Remote Similarity	NPC151403
0.5167	Remote Similarity	NPC240695
0.5167	Remote Similarity	NPC261952
0.5167	Remote Similarity	NPC605171
0.5152	Remote Similarity	NPC488630
0.5152	Remote Similarity	NPC488625
0.5152	Remote Similarity	NPC488626
0.5098	Remote Similarity	NPC474705
0.5082	Remote Similarity	NPC93794
0.5082	Remote Similarity	NPC488632
0.5082	Remote Similarity	NPC473504
0.5082	Remote Similarity	NPC81778
0.5082	Remote Similarity	NPC40066
0.5082	Remote Similarity	NPC47937
0.5079	Remote Similarity	NPC602738
0.5077	Remote Similarity	NPC89001

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC480082 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6601
0.1-0.2	2477
0.2-0.3	71
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data